Abstract
A novel magnetic Co nanoparticle catalyst was prepared by coating Fe304magnetic nanoparticles with tetraethyl orthosilicate functionalized with (3-chloropropyl)trimethoxysilane and 2-amino-5-mercapto-1,3,4-thiadiazole ligands followed by complexation with Co(OAc)4. The catalyst was then characterized and applied for the synthesis of various tetrazoles by the reactions of amines with sodium azide and triethyl orthoformate in solvent-free conditions at 100°C.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Katritzky, A.R., Rees, C.W., and Scriven, E.F., Comprehensive Heterocyclic Chemistry II, Oxford: Pergamon, 1996.
Butler, R.N., Adv. Heterocycl. Chem., 1977, vol. 21, p. 323. https://doi.org/10.1016/S0065-2725(08)60735-7
Wittenberger, S.J., Org. Prep. Proceed. Int., 1994, vol. 26, p. 499. https://doi.org/10.1080/00304949409458050
Herr, R.J., Bioorg. Med. Chem., 2002, vol. 10, p. 3379, https://doi.org/10.1016/S0968-0896(02)00239-0
Zhilin, A.Y., Ilyushin, M.A., Tselinskii, I.V., Kozlov, A.S., and Lisker, I.S., Russ. J. Appl. Chem., 2003, vol. 76, p. 572. https://doi.org/10.1023/A%3A1025778918488
Finnegan, W.G., Henry, R.A., and Lieber, E., J. Org. Chem., 1953, vol. 18, p. 779. https://doi.org/10.1021/jo50013a002
Garbrecht, W.L. and Herbst, R.M., J. Org. Chem., 1953, vol. 18, p. 1014. https://doi.org/10.1021/jo50014a016
Henry, R.A., Finnegan, W.G., and Lieber, E., J. Am. Chem. Soc, 1954, vol. 76, p. 88. https://doi.org/10.1021/ja01630a024
Svetlik, J., Hrusovsky, L., and Martvon, A., Collect. Czech. Chem. Commun., 1979, vol. 44, p. 2982. https://doi.org/10.1135/ccccl9792982
Batey, R.A. and Powell, D.A., Org. Lett., 2000, vol. 2, p. 3237. https://doi.org/10.1021/ol006465b
Stolle, R. and Heintz, K., J. Prakt. Chem., 1937, vol. 147, p. 286. https://doi.org/10.1002/prac.19371471002
Miller, A.E., Feeney, D.J., Ma, Y., Zarcone, L., Aziz, M.A., and Magnuson, E., Synth. Commun., 1990, vol. 20, p. 217. https://doi.org/10.1080/00397919008052286
Katritzky, A.R., Rogovoy, B.V., and Kovalenko, K.V., J. Org. Chem., 2003, vol. 68, p. 4941. https://doi.org/10.1021/jo0266543
Klich, M. and Teutsch, G., Tetrahedron, 1986, vol. 42, p. 2677. https://doi.org/10.1016/S0040-4020(01)90553-8
Henry, R.A., Finnegan, W.G., and Lieber, E., J. Am. Chem. Soc, 1955, vol. 77, p. 2264. https://doi.org/10.1021/ja01613a071
Ley, S.V., Baxendale, I.R., Bream, R.N., Jackson, P.S., Leach, A.G., Longbottom, D.A., Nesi, M., Scott, J.S., Storer, R.I., and Taylor, S.J., J. Chem. Soc. Perkin Trans. 1, 2000, vol. 1, p. 3815. https://doi.org/10.1039/b006588i
Gorte, R.J., Catal. Lett., 1999, vol. 62, p. 1. https://doi.org/10.1023/A:1019010013989
Ariannezhad, M., Habibi, D., and Heydari, S., Russ. J. Org. Chem., 2019, vol. 55, p. 1591. https://doi.org/10.1016/j.poly.2018.12.037
Acknowledgments
The authors are grateful to the Islamic Azad University (Faculty of Sciences, Arak Branch, Arak, Iran), Islamic Azad University (Faculty of Sciences, Hamedan Branch, Hamedan, Iran), and Bu-Ali Sina University (Hamedan, Iran) for financial support of this work.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Sarrafioun, F., Jamehbozorgi, S. & Ramezani, M. Synthesis of Tetrazoles Catalyzed by Novel Cobalt Magnetic Nanoparticles. Russ J Org Chem 55, 1777–1784 (2019). https://doi.org/10.1134/S1070428019110216
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019110216